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- W2313307429 abstract "Two novel rearrangements of nitroso alkanes, one intramolecular acid catalyzed cleavage reaction and the other ring enlargement during hydride reduction, are described. Aminium radical initiated addition to norbornene under nitrogen gave cis-exo- and trans-2-nitroso-3-ammonium norbornanes in a good yield. Whereas the trans isomer underwent the usual nitroso group reactions, i.e., tautomerization, dimerization, and HNO addition, the cis-exo isomer and its hydroxy analog cleaved extremely readily to give 1,3-bisformylcyclopentane derivatives. The stereoelectronic driving force in this cleavage is interpreted as the intramolecular proton transfer and the electron reorganization via a cyclic transition state. Metal hydride reduction of the trans isomer was accompanied by ejection of the neighboring amino group and an expansion of the ring to form an azabicyclic compound. A sequence involving an intramolecular displacement to form aziridine followed by the reductive cleavage is proposed." @default.
- W2313307429 created "2016-06-24" @default.
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- W2313307429 date "1975-10-15" @default.
- W2313307429 modified "2023-09-27" @default.
- W2313307429 title "Photoreaction of Nitroso Compounds in Solution. Part XXXI. Mechanisms of Intramolecular Acid Catalyzed Cleavage Reactions and a Hydride Initiated Rearrangement of <i>C</i>-Nitroso Alkanes" @default.
- W2313307429 doi "https://doi.org/10.1139/v75-427" @default.
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